EP2674034A1 - Verfahren zur herstellung von krillöl und in diesem verfahren hergestelltes krillöl - Google Patents

Verfahren zur herstellung von krillöl und in diesem verfahren hergestelltes krillöl Download PDF

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Publication number
EP2674034A1
EP2674034A1 EP11858111.5A EP11858111A EP2674034A1 EP 2674034 A1 EP2674034 A1 EP 2674034A1 EP 11858111 A EP11858111 A EP 11858111A EP 2674034 A1 EP2674034 A1 EP 2674034A1
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EP
European Patent Office
Prior art keywords
krill
proteases
enzyme reaction
astaxanthin
phospholipids
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
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EP11858111.5A
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English (en)
French (fr)
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EP2674034B1 (de
EP2674034A4 (de
Inventor
Sang Su Lee
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ALPHA B&H CO., LTD.
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Dae Duck FRD Co Ltd
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Priority to PL11858111T priority Critical patent/PL2674034T3/pl
Publication of EP2674034A1 publication Critical patent/EP2674034A1/de
Publication of EP2674034A4 publication Critical patent/EP2674034A4/de
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B1/00—Production of fats or fatty oils from raw materials
    • C11B1/10—Production of fats or fatty oils from raw materials by extracting
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A23D9/013—Other fatty acid esters, e.g. phosphatides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B1/00—Production of fats or fatty oils from raw materials
    • C11B1/02—Pretreatment
    • C11B1/025—Pretreatment by enzymes or microorganisms, living or dead
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y304/00—Hydrolases acting on peptide bonds, i.e. peptidases (3.4)
    • C12Y304/21—Serine endopeptidases (3.4.21)
    • C12Y304/21014—Microbial serine proteases (3.4.21.14)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y304/00—Hydrolases acting on peptide bonds, i.e. peptidases (3.4)
    • C12Y304/24—Metalloendopeptidases (3.4.24)
    • C12Y304/24004—Microbial metalloproteinases (3.4.24.4)

Definitions

  • the present disclosure relates to krill oil and a method for manufacturing the krill oil, more particularly, to a method for manufacturing krill oil from krill using proteases and ultra-high pressure reactor and krill oil manufactured by the method.
  • Antarctic krill (E. superba) belonging to krill are estimated to have 2 billion tons of inhabitation amount and 30 million tons of fair catch and the world pays attention to the use and development of the krill.
  • the krill as the main prey of marine animals including whales are located in the lowest in the food chain in the Antarctic Ocean and are less polluted, so the krill are very useful in food, cosmetics, pharmaceuticals, etc.
  • the krill include nutritionally good quality of protein and lipids.
  • the fresh krill include up to about 10% of lipids.
  • the lipids of the krill include about 40% of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), which are omega-3 highly unsaturated fatty acids and about 40 - 50% of phospholipids.
  • EPA eicosapentaenoic acid
  • DHA docosahexaenoic acid
  • the krill include astaxanthin that is antioxidant of fat soluble carotenoids.
  • Organic solvent extraction method and supercritical extraction method are used as methods for extracting the lipids, which have high nutritional value, from the krill.
  • the organic solvent extraction method needs a large amount of organic solvent as well as a lot of time for extraction.
  • the organic solvent may not be entirely removed and still remain in krill oil, and wastewater may be produced by the organic solvent.
  • supercritical extraction method supercritical equipment is too expensive and difficult to operate.
  • the present disclosure provides a method for manufacturing krill oil at low cost. Manufacturing cost can be reduced by extracting effective ingredients of krill not using expensive supercritical equipment and manufacturing krill oil.
  • the present disclosure also provides a method for manufacturing krill oil eco-friendly.
  • the krill oil can be manufactured by extracting the effective ingredients of the krill eco-friendly not using toxic organic solvents such as acetone, hexane, etc.
  • the present disclosure provides krill oil manufactured using the above method.
  • the present disclosure provides a method for manufacturing krill oil comprising preparing krill, adding protease to the kirll and performing enzyme reaction, extracting eicosapentaenoic acid, docosahexaenoic acid, phospholipids, and astaxanthin from the krill after performing the enzyme reaction, and mixing the extracted eicosapentaenoic acid, docosahexaenoic acid, phospholipids, and astaxanthin.
  • the protease may comprise one or more chosen from serine alkaline proteases and metallo neutral proteases.
  • the serine alkaline proteases may comprise proteases separated from Bacillus licheniformis and the metallo neutral proteases may comprise proteases separated from Bacillus subtillis and Bacillus amyloliquefaciens.
  • the enzyme reaction may be performed in an ultra-high pressure reactor.
  • reaction pressure is 10 - 300MPa
  • reaction temperature is 50 - 60°C
  • reaction time is 3 - 24hours.
  • the krill including the protease are liquefied.
  • the pH of the liquefied krill may be adjusted to be 3.0 - 5.0.
  • the liquefied krill may be filtered to be separated as filtrate and sludge, the eicosapentaenoic acid, the docosahexaenoic acid, and the phospholipids may be extracted by centrifugation of the filtrate, and the astaxanthin may be extracted by cleaning the sludge with ethanol.
  • the preparing of the krill may comprise pulverizing the krill.
  • the pH of the krill is adjusted to be 7.5 - 9.0.
  • the present disclosure provides krill oil manufactured by the method.
  • the krill oil may comprise 14 - 18wt% of eicosapentaenoic acid, 8 - 12wt% of docosahexaenoic acid, 35 - 45wt% of phospholipids, and 70 ⁇ 170ppm of astaxanthin.
  • FIG. 1 illustrates a process for manufacturing krill oil according to an embodiment of the present invention.
  • frozen or freeze-dried krill are thawed and salt is removed from the krill by washing.
  • the krill are pulverized.
  • the krill may be pulverized as a size of about 0.5cm.
  • protease is added to the pulverized krill.
  • the protease and the krill may be mixed and stirred for 30min - 1hr.
  • the protease may comprise one or more chosen from serine alkaline proteases and metallo neutral proteases.
  • the serine alkaline proteases may comprise proteases separated from Bacillus licheniformis.
  • the metallo neutral proteases may comprise proteases separated from Bacillus subtillis and Bacillus amyloliquefaciens.
  • the present inventors have conducted many experiments using various proteases and have found that lipids, phospholipids, and astaxanthin can be effectively extracted from krill by the serine alkaline proteases separated from Bacillus licheniformis and/or the metallo neutral proteases separated from Bacillus subtillis and Bacillus amyloliquefaciens.
  • the protease may be added in an amount of 0.1 - 3.0 parts by weight parts per 100 parts by weight of the krill. In case where an addition amount of the protease is less than 0.1 parts by weight, the amount of the protease is too low compared to the amount of protein of the krill, so enzyme reaction may be delayed or hydrolysis of the protein may be incomplete. In case where an addition amount of the protease is more than 3.0 parts by weight, the hydrolysis of the protein may be fast but the protease is added than necessary compared to the amount of the protein so over-use of the protease may have a bad influence on flavor of the krill and manufacturing costs may increase.
  • the pH of the krill may be adjusted to be 7.5 ⁇ 9.0.
  • the protease may be activated in the range of the above pH.
  • Enzyme reaction is performed in the krill. Protein of the krill can be hydrolyzed by the enzyme reaction.
  • the enzyme reaction may be performed in an ultra-high pressure reactor. In the ultra-high pressure reactor, the reactor pressure may be 30 ⁇ 300MPa, the reactor temperature may be 50 - 60°C, and the reaction time may be 3 - 24hours. In the ultra-high pressure reactor, the krill can be liquefied and the enzyme reaction can be performed in the liquefied krill.
  • the pH of the liquefied krill may be adjusted to be 3.0 ⁇ 5.0.
  • the pH can be adjusted by adding 2 - 4 parts by weight of citric acid and/or ascorbic acid per 100 parts by weight of the krill and letting the krill be stationary for 30min - 1hr.
  • a mixture of water and amino acids formed by the hydrolysis of the protein and lipids can be separated each other by adjusting the pH.
  • the liquefied krill are filtered to be separated as filtrate and sludge.
  • the filtrate is filtered using 100 and 200 mesh sieve and the sludge including the shell of the krill and so on can be separated.
  • the filtrate is centrifuged and lipids and phospholipids can be extracted.
  • the lipids may comprise eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA).
  • the centrifugation speed may be 3000 - 13000rpm.
  • the amino acids and peptides can be collected from the filtrate by the centrifugation.
  • Krill extract can be manufactured by decompressing and concentrating the amino acids and the peptides.
  • the sludge is cleaned with 95% ethanol and astaxanthin can be extracted.
  • the ethanol may be added in the amount of 200 - 300 parts by weight per 100 parts by weight of the slugde.
  • Krill oil can be manufactured by mixing the lipids, the phospholipids and the astaxanthin and by decompressing and concentrating them.
  • the ethanol can be collected and the water can be removed in the decompressing and concentrating process.
  • the temperature in the decompressing and concentrating process may be 45 - 65°C.
  • FIG. 2 illustrates a process for manufacturing krill oil according to other embodiment of the present invention.
  • the enzyme reaction may be performed in a conventional reactor rather than the ultra-high pressure reactor.
  • Krill were prepared by thawing frozen krill and washing the thawed krill with water to remove salt and impurities and freeze-dried krill were prepared.
  • the analysis of the nutritional composition is shown in Table 1 below.
  • Krill samples were prepared by pulverizing frozen krill with a mixer. Distilled water and proteases were added to the krill samples. The krill samples were hydrolyzed at the ultra-high pressure of 30, 50, 70, and 100MPa and at the temperature of 55°C and were liquefied. Mixed liquid of serine alkaline proteases separated from Bacillus licheniformis and metallo neutral proteases separated from Bacillus subtillis and Bacillus amyloliquefaciens was used as the above proteases. The serine alkaline proteases and the metallo neutral proteases may be separated by low-temperature water extraction method.
  • the distilled water was added in the amount of 100 parts by weight and the proteases were added in the amount of 1 parts by weight per 100 parts by weight of the krill.
  • the hydrolyzed and liquefied products were filtered to be separated as filtrate and sludge.
  • the filtrate was centrifuged and lipids and phospholipids were extracted.
  • the sludge was cleaned with ethanol and astaxanthin was extracted.
  • Krill oil was manufactured by mixing the lipids, the phospholipids and the astaxanthin and by decompressing and concentrating them. The recovery ratios of the lipids are shown in Table 2 below.
  • the recovery ratios of the lipids were more than 30%.
  • the recovery ratios of the lipids were more than 80%.
  • the recovery ratios of the lipids were more than 90%.
  • the reaction time was more than 18 hours, the recovery ratios of the lipids were more than 95% regardless of the size of the pressure.
  • Krill samples were prepared by pulverizing frozen krill with a mixer. Distilled water and proteases were added to the krill samples. The krill samples were hydrolyzed for 12hours at atmospheric pressure and at the temperature of 55°C and were liquefied. Mixed liquid of serine alkaline proteases separated from Bacillus licheniformis and metallo neutral proteases separated from Bacillus subtillis and Bacillus amyloliquefaciens was used as the above proteases.
  • the distilled water was added in the amount of 100 parts by weight and the proteases were added in the amount of 1 parts by weight per 100 parts by weight of the krill.
  • the hydrolyzed and liquefied products were filtered to be separated as filtrate and sludge.
  • the filtrate was centrifuged and lipids and phospholipids were extracted.
  • the sludge was cleaned with ethanol and astaxanthin was extracted.
  • Krill oil was manufactured by mixing the lipids, the phospholipids and the astaxanthin and by decompressing and concentrating them.
  • Krill samples were prepared by pulverizing frozen krill with a mixer. Distilled water was added to the krill samples. The krill samples were hydrolyzed for 12hours at the ultra-high pressure of 100MPa and at the temperature of 55°C and were liquefied. The distilled water was added in the amount of 100 parts by weight per 100 parts by weight of the krill. Proteases were not added unlike the above Example 5 and krill oil was manufactured using an ultra-high pressure reactor.
  • Krill samples were prepared by pulverizing frozen krill with a mixer. Distilled water and proteases were added to the krill samples. The krill samples were hydrolyzed for 12hours at the ultra-high pressure of 100MPa and at the temperature of 55°C and were liquefied. Krill oil was manufactured by the same method as the above Example 5 except using an ultra-high pressure reactor.
  • Krill samples were prepared by pulverizing freeze-dried krill with a mixer. Distilled water and proteases were added to the krill samples. The krill samples were hydrolyzed for 12hours at the ultra-high pressure of 100MPa and at the temperature of 55°C and were liquefied. Krill oil was manufactured by the same method as the above Example 7 except using the freeze-dried krill.
  • Nutritional composition of the krill oil manufactured in the above Examples 5 to 8 was analyzed. The results are shown in Table 3 below.
  • the analysis method for the nutritional composition is as follows.
  • the krill oil may comprise 14 - 18wt% of eicosapentaenoic acid, 8 - 12wt% of docosahexaenoic acid, 35 - 45wt% of phospholipids, and 70 ⁇ 170ppm of astaxanthin.

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EP11858111.5A 2011-02-11 2011-07-21 Verfahren zur herstellung von krillöl und in diesem verfahren hergestelltes krillöl Active EP2674034B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PL11858111T PL2674034T3 (pl) 2011-02-11 2011-07-21 Sposób wytwarzania oleju z kryla i olej z kryla wytwarzany tym sposobem

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KR1020110012550A KR101045258B1 (ko) 2011-02-11 2011-02-11 크릴 오일 제조 방법 및 상기 방법에 의해 제조된 크릴 오일
PCT/KR2011/005386 WO2012108593A1 (ko) 2011-02-11 2011-07-21 크릴 오일 제조 방법 및 상기 방법에 의해 제조된 크릴 오일

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EP2674034A1 true EP2674034A1 (de) 2013-12-18
EP2674034A4 EP2674034A4 (de) 2016-07-20
EP2674034B1 EP2674034B1 (de) 2018-04-18

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US (1) US8624046B2 (de)
EP (1) EP2674034B1 (de)
JP (1) JP5860482B2 (de)
KR (1) KR101045258B1 (de)
CN (1) CN103501623B (de)
CA (1) CA2827085C (de)
NO (1) NO2674034T3 (de)
PL (1) PL2674034T3 (de)
WO (1) WO2012108593A1 (de)

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JP7021953B2 (ja) * 2015-12-24 2022-02-17 株式会社 ビーアンドエス・コーポレーション エーテル型グリセロリン脂質の製造方法
JP6632888B2 (ja) * 2016-01-07 2020-01-22 株式会社マリン大王 イサダオイルおよびその製造方法
CN107080769A (zh) * 2017-05-17 2017-08-22 王茹 一种治疗各种慢性疾病的天然药物及医用配方食品
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KR20220007435A (ko) 2020-07-10 2022-01-18 주식회사 엘아이티코퍼레이션 오메가-3 지방산이 풍부한 크릴오일의 제조방법 및 이에 의해 제조된 크릴오일
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GB0813598D0 (en) * 2008-07-24 2008-09-03 Pharma Marine As Process
ES2639959T3 (es) * 2008-09-12 2017-10-30 Rimfrost Technologies As Procedimiento de reducción del contenido de fluoruro cuando se producen concentrados proteínicos a partir de kril
CA2738282C (en) * 2008-09-26 2016-05-24 Nippon Suisan Kaisha, Ltd. Method for concentrating lipids
KR100951727B1 (ko) * 2008-09-30 2010-04-07 주식회사 유맥스 크릴로부터 유용성분 추출분리방법 및 관련 제품
KR20100038029A (ko) * 2008-10-02 2010-04-12 인성실업(주) 초임계 추출에 의하여 크릴 오일을 생산하는 방법 및 오메가-3 지방산 함량이 높은 크일 오일 조성물
KR101024491B1 (ko) * 2008-12-31 2011-03-31 인성실업(주) 해양 동물로부터 지질을 추출하는 방법
WO2010097701A1 (en) * 2009-02-26 2010-09-02 Aker Biomarine Asa Low viscosity phospholipid compositions
CN101933596B (zh) * 2010-09-03 2012-12-26 华南农业大学 一种以虾头和虾壳为原料酿制虾油的方法

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019111055A1 (en) * 2017-12-04 2019-06-13 Rimfrost Technologies Method for producing a protein phospholipid complex from a crustacean catch
CN111432654A (zh) * 2017-12-04 2020-07-17 雾凇科技有限公司 从甲壳类捕获物中生产蛋白质磷脂复合物的方法

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CA2827085C (en) 2015-08-11
NO2674034T3 (de) 2018-09-15
JP2014509339A (ja) 2014-04-17
EP2674034B1 (de) 2018-04-18
CN103501623B (zh) 2015-09-16
CA2827085A1 (en) 2012-08-16
US8624046B2 (en) 2014-01-07
JP5860482B2 (ja) 2016-02-16
PL2674034T3 (pl) 2018-09-28
EP2674034A4 (de) 2016-07-20
CN103501623A (zh) 2014-01-08
WO2012108593A1 (ko) 2012-08-16
US20130274496A1 (en) 2013-10-17

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